


My First

by theinsandoutsofcastiel



Category: Supernatural
Genre: F/M, Multiple Orgasms, NSFW, Oral, virgin!reader
Language: English
Status: Completed
Published: 2016-12-18
Updated: 2016-12-18
Packaged: 2018-09-09 15:46:29
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,657
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/8897884
Author URL: https://archiveofourown.org/users/theinsandoutsofcastiel/pseuds/theinsandoutsofcastiel
Summary: Hi, I love your one shots and was wondering if you could do a smutty young/inexperienced reader (like 18 or 19)xdean where she’s known him her whole life & he’s her best friend & she’s in love with him and wants him to be her first so she asks him one night in the bunker? Thanks :) and sorry it’s so specific AND Can you do a oneshot where the reader is a hunter dating Dean & she loses her virginity to him? (Maybe she lives at the bunker with the boys?) (Also maybe she’s self conscious before?). Sorry for the length, love your blog btw!! ❤️ AND Can I please request a fic where it’s the reader’s first time with Dean and she’s nervous so Dean gets her to open up to him and tell him what she wants.





	

Warnings: Language, smut, virgin!Reader, oral, multiple orgasms

Fic:

“Dean, I think I’m ready,” you tell him. His arm is wrapped around you, holding you close to his side.

“Ready for what?” Dean asks, pulling his attention away from the T.V. screen to look down at you.

“You know,” you answer, letting him fill in the blank. You push yourself up on the sofa and wait for him to respond.

“You mean you’re ready to have sex?” Dean asks, finally understanding what you were talking about.

“Yeah,” you answer, your cheeks heating up.

“What brought this on all of the sudden?” Dean questions.

“It’s just … I think I’m ready,” you reply, “We’ve been together for a while now. I’ve known you my whole life and I trust you more than I’ve ever trusted anyone else. You’re my best friend, and I love you, and I want you to be my first.” Your cheeks feel even hotter than they did before and you look away in embarrassment.

“Y/N, look at me,” Dean says gently as he hooks two fingers beneath your chin and brings your gaze back to his, “Before we take things any further, I want you to know that you’re ready, not just think it. I don’t mind waiting for you, you know that.”

“I know,” you tell him, “But I want you. I’m ready, Dean. Please?” Dean grabs the remote and turns of the T.V. before tossing the remote back onto the table.

“You’re sure about this?” Dean asks, “About me?”

“Yes,” you answer, “I’m sure.”

“Come on,” Dean says as he takes your hand, “Your room or mine?”

“I, um, whichever is fine,” you answer.

“Y/N, I want you to be comfortable,” Dean tells you, “So which room would you prefer?”

“Well … you do have the memory foam mattress,” you say nervously, “So, yours I guess.”

“Ok,” Dean says gently. He guides you from the sofa and leads you to his room, closing the door after you step inside. “I know you’re new to this,” Dean says as he wraps you up in his arms, “So I want you to know it’s ok to tell me to stop. If there’s anything I do that you don’t like, all you have to do is say so and I’ll never do it again, ok?” You hum and nod in response.

Dean cups your cheek, tilting your head and capturing your lips. He was starting slow, beginning with something familiar in order to ease you into what’s to come. You’d become accustomed to the feel of his soft lips moving against yours, his tongue seeking entrance to your mouth. Dean’s hand slides back into your hair as he deepens the kiss, his other arm wraps around your waist, pulling you to him as he guides you towards his bed. He sits on the edge of the mattress and guides you to sit next to him.

The feeling of Dean’s hands exploring your body is familiar as well. He would often run his hands up your arms or along your sides. Even so, you gasp as his fingertips slip beneath your shirt and press gently against your skin. “Is that alright?” Dean asks, breaking the kiss. You nod, encouraging him to continue.

Dean slowly tugs the hem of your shirt higher and higher until he’s pulled the material over your head. As the cold air hits your skin, you suddenly feel self conscious. You cross your arms across your body, trying to hide yourself as best you can.

“Y/N, what’s wrong?” Dean asks, reaching out and running a hand along your arm.

“I’m just nervous,” you admit.

“You have nothing to be nervous about,” Dean assures you, “If you want to stop, we don’t have to go any further.”

“No, I don’t want to stop,” you tell him.

“Ok,” Dean says gently, pausing for a moment before continuing, “Y/N, you don’t have to hide yourself from me. I have seen you naked before.”

“Not completely naked,” you protest, “And never in a situation like this.”

“Fare enough,” Dean admits, “Would it help if you saw me naked first?”

“I -” you stumble, “Well, maybe.”

Without hesitation, Dean shrugs his plaid shirt from his shoulders and pulls his t-shirt over his head. Standing from the bed, Dean opens the front of his pants, pushing them down along with his boxers. You draw your bottom lip between your teeth as you look him over. His cock is already half hard and you can’t stop the groan from escaping your lips.

“What?” Dean laughs.

“I lied,” you answer, “Seeing you first doesn’t help at all.”

“Y/N,” Dean sighs as he sits beside you again, “Do you know how beautiful I think you are, how perfect?” When you don’t answer, Dean continues, “I think you’re gorgeous, body, mind, and soul. I love you like I’ve never loved anyone before.”

“It’s just nervousness,” you tell him.

“Like I said, you have nothing to be nervous about,” Dean says, “You see what you’ve already done to me right?” He reaches out and brushes your hair behind your ear. Slowly, you let your hands fall away from you and you reach behind you to unhook your bra. You stand from the bed as you let the material fall from your body. “Damn,” Dean whispers as he watches you wiggle out of your pants and panties. He runs his hands down your sides before pulling you to his lap. “You’re gorgeous,” Dean tells you as he places butterfly kisses along your collarbone. His hands explore your body, callused fingertips raising goosebumps on your skin as he traces your curves.

You run your hands along his chest and up the sides of his neck before tangling them into his hair. The warmth of his body sinks into you and you ease into the feeling of his skin against yours. Dean’s lips move up from your collarbone to find your pulse point, placing kisses as he goes. “Dean,” you mutter. You can feel him growing harder and harder beneath you.

“Tell me what you want,” Dean requests.

“I - I don’t know,” you answer, flustered.

“What turns you on?” Dean asks, “What do you think about when you’re alone, touching yourself?”

“I, well, I don’t know, I think about you I guess,” you answer, stumbling over your words. You hadn’t expected him to ask you a question like that.

“You guess?” Dean chuckles.

“Yeah, um, I imagine pleasing you,” you say shyly.

“How?” Dean presses.

“Dean,” you laugh nervously, looking away out of embarrassment.

“Y/N,” Dean says gently as he lifts your gaze to his again, “Do you wanna know what I think about when I masturbate?” You swallow thickly before nodding wordlessly. “I think about touching you,” Dean continues, “My hands all over your body, exploring every inch, squeezing your breasts. Your back arches, pushing them into my hands.” As Dean speaks, he acts out his words, hands trailing over your body before stopping on your breasts. Your back arches just as he had described. “I imagine kissing every inch of your body,” Dean adds, “I imagine tasting you, burying my head between your legs and eating you out until you’re screaming my name.”

“Dean,” you gasp, but this doesn’t stop him.

“I pretend that my hand is yours, stroking my cock,” he tells you, “You’d kiss me as you move your hand up and down. Maybe you’d kiss lower and lower on my body until you take me into your mouth.”

“I wouldn’t even know what to do,” you admit. Dean laughs quietly.

“You’d be perfect,” Dean tells you, “I have no doubt.”

“A-and what about after?” you ask him.

“What would you want to happen after?” Dean asks.

“I’d want you to fuck me,” you blurt out without thinking, “Dean, I want you to fuck me.” Dean grins and you instantly feel the blush rising to your cheeks again.

“Well aren’t you eager?” Dean teases, “But we’re going to go a little slower than that.” One of his hands slides down your body and makes its way between your legs. You gasp as pleasure shoots through you, Dean’s rough fingers finding your clit. Your hips instantly rock towards his hand, seeking more friction.

“Dean, I, oh fuck,” your words become moans as his fingers slide into you. His thumb presses to your clit as he moves his fingers inside you, scissoring and curling them. You cry out as he finds just the right spot, your hips bucking towards him. His name falls from your lips as you fist your hands into his hair.

“You’re so wet,” Dean mutters against your skin as he places gentle kisses up your neck. He kisses your cheeks as his free hand splays across your back, encouraging you to ride his fingers. You moan as Dean’s rough fingers curl against your g-spot, the sensation causing your stomach to twist in pleasure. Dean brings you closer and closer to the edge, your muscles tensing as the pressure in your stomach threatens to spill over.

“Dean,” you whimper, pressing your forehead to his. Dean smiles before capturing your lips. At the same moment, he crooks his fingers in a come hither motion, sending you over the edge. You moan as your walls squeeze Dean’s fingers, but the sounds are muffled by Dean’s lips. He holds you close as your muscles tense and relax, his fingers working you through your high. You clutch at him, trying to hold on to something solid as pleasure washes over you.

“That’s it,” Dean encourages as you rock your hips in an attempt to prolong your high. You slump against him and Dean holds you close, pressing butterfly kisses to your neck and shoulder. “How was that?” Dean asks as he pulls his fingers from you.

“Perfect,” you tell him, making him laugh.

“Lie down,” Dean instructs gently, but you shake your head in protest, “Why not?” You draw your bottom lip between your teeth as you sit back.

“I have something I want to try first,” you tell him. Dean watches as you move from his lap, placing kisses down his chest as you sink to the floor.

“Y/N, you don’t have to do this,” Dean says as you push his legs apart and settle between them. His hand reaches down to cup your cheek, thumb running along your skin.

“I want to,” you tell him. You tried to sound confident even though you were nervous. Dean swallows thickly as you run your hands up his thighs. Sliding one hand higher, you trace your fingertips along the shaft of his cock.

“Y/N,” Dean gasps as you run your thumb over his leaking slit. You collect the precum that’s beaded there and use it to slick his cock. Dean groans as you begin stroking him, his cock twitching in your hand.

Looking up at him through your lashes, you watch the pleasure wash over his expression as you take his tip between your lips. You hum at the salty taste of his precum, making his hips buck lightly. Dean’s eyes flutter shut and his lips part as you pump your hand over his length and swirl your tongue around his tip. One of his hands twists into your hair, his other fisting in the sheets.

“A-am I doing this right?” you ask him, pulling away.

“Y/N, Baby, you’re doing great,” Dean answers, “Don’t stop, please.”

“I mean it,” you tell him, “I’ve never done this before. Tell me what you like.”

“You - you can tease a little if you want,” Dean instructs.

“Like this?” you ask him as you fondle his balls and lean in, placing open mouth kisses up his shaft.

“Fuck,” Dean gasps, “That’s good.” He can’t take his eyes off you. “Y/N, I need you to -” he begins, but his words are cut off when you take him into your mouth again. The look of pure pleasure returns to his face as you swirl your tongue around his tip. “I need you to take more if you can,” Dean groans.

You hum before taking more of him into your mouth. His tip hits the back of your throat and you gag slightly before easing into the feeling. You begin bobbing your head up and down, giving him more friction.

“Oh, Y/N,” Dean groans, his hand tightening in your hair, “Use your tongue, Baby.” You take his instruction, using your tongue to tease the underside of his cock. He tugs your hair lightly, guiding you as you bob your head. “Baby, I need you to suck,” Dean groans. You flick your eyes up, watching him through your lashes as you hollow your cheeks around him.

Dean’s jaw goes slack and his head tips back. You hum, sending vibrations straight down his length. The sensation makes his hips buck from the bed. His cock throbs and twitches in your mouth, his groans getting louder.

“Y/N, Baby, fuck I’m gonna cum,” Dean warns. You take this to mean that he likes what you’re doing and you decide not to stop. “Y/N, oh fuck,” he groans, his jaw clenching as his cock twitches hard. Even though he had warned you, the first ribbon of cum takes you by surprise as it hits the back of your throat. 

Dean grunts and groans as his cock pulses, spilling himself against your tongue. You lick and suck, drinking down every drop he has to give you. Dean leans back and lets his hand go slack in your hair as you work him through his high, milking him for all he’s worth. You pull off him with a pop before sitting back on your heels.

“Was I ok?” you ask him, looking up at him nervously. Dean looks down at you with bliss glazed eyes, a blissful smile on his lips.

“Y/N, that was fucking awesome,” Dean tells you, “Come here.” Dean reaches for your arms and pulls you to his lap. His lips capture yours and he kisses you deeply. You break the kiss and squeal as Dean lifts you up and lies you down against the bed, his body caging you beneath him.

“I love you,” you tell him, caressing his cheek. Dean smiles as he leans into your touch.

“I love you too,” Dean says. He leans down and presses kisses down your neck and along your collarbone.

“Dean, what are you doing?” you ask him as he kisses lower and lower on your body.

“Returning the favor,” Dean says with a smirk. He spreads your legs and settles between them, leaving kisses up and down your thighs. You gasp as his lips ghost over your clit. Dean looks up at you through his lashes as he leans in and leaves a long lick up the length of your entrance.

“Dean,” you moan, fisting your hands into the pillows beside your head. Dean sucks your folds between his lips and draws them out before teasing his tongue inside you. Your hips lift from the bed and Dean slips his hands beneath you, encouraging you to grind your hips against him.

“That’s it,” Dean encourages, mumbling against you. He nudges your clit with his nose, making you whimper as pressure builds in your stomach. You can’t stop yourself from squirming against the bed as Dean swirls his tongue against your walls, exploring as much of you as he can. Each little action draws you closer and closer to your end. “You taste so good,” Dean mumbles against you. You can feel a blush rise to your cheeks as the vibrations he makes travel to your core.

Dean rocks his hips against the bed as he eats you out, seeking friction for himself as he brings you right to the edge. “Dean,” you moan, “Oh, Dean.” Reaching down, you fist a hand into Dean’s hair as your back arches from the bed. Dean pulls his tongue from you, but he doesn’t give you much time to process the loss. He moves one of his hands and slides three fingers into you as he sucks your clit between his lips. He flicks your clit with his tongue as he crooks his fingers inside you, sending you right over the edge. “Dean!” you cry out as the pressure in your stomach releases.

Your hands tighten in the sheets and in Dean’s hair, trying to hold on to something as Dean works you through your high. His fingers work inside you as his tongue laps up everything you have to give him. Your body shudders as pleasure courses through you; the aftershocks of your orgasm have your walls clamping down around Dean’s fingers. “You like that?” Dean asks, his movements slowing.

“Mmm,” you hum, “Dean.” You melt into the bed as you begin to come down from your high. Dean pulls his fingers from you and brings them to his lips, licking them clean one by one. As soon as they’re clean, he begins kissing his way back up your body, caging you beneath him once again.

“I love you, Y/N,” Dean whispers before kissing the sweet spot behind your ear.

“I love you too, Dean,” you reply as you run your hands through his hair and down his back, “I want you.”

“Are you sure you’re ready?” Dean asks between kisses.

“Yes,” you answer, “I’m sure.” Dean props himself above you, looking down at you lovingly before leaning in to kiss your lips.

“Hang on just a second, ok?” Dean asks as he pulls away and rolls to the side. He opens his nightstand drawer and pulls out a box of condoms, pulling one out before tossing the box onto the nightstand.

“You just keep those lying around?” you ask him.

“Better safe than sorry,” Dean shrugs as he tears open the package. You draw your bottom lip between your teeth as you watch him roll the condom over his length. “Tell me if you need me to stop,” Dean says as he settles himself above you. You nod in understanding.

You let your eyes fall shut as Dean kisses you deeply, distracting you as he lines himself up with your entrance. His hand slides down your leg and hooks behind your knee, drawing it up around his waist as he sinks into you slowly. He fills you inch by throbbing inch, allowing you to adjust to the feeling of having him inside you before pushing in further. You moan and whimper his name, your fingertips digging into the skin of his back as you desperately try to pull him closer.

“Is that alright?” Dean asks, placing kisses against your neck as he sheaths himself completely inside you.

“Yes,” you moan, your head tipping back against the pillows as you lift your hips, “I need you to move, please.” He was perfect, stretching you and hitting all the right spots. Dean smiles against your skin before pulling back and slowly pushing into you again.

You drag your nails lightly down his back as you lift your hips in time with Dean’s slow thrusts. His love and desire for you is evident in his every action. Each touch, each kiss, each thrust sets your senses on fire. You’re consumed by him and it’s unlike anything you’ve ever felt before.

“Y/N,” Dean groans again and again. His fingertips dip into your skin as his thrusts become slightly erratic. “Damn, you’re perfect,” he mutters against your skin. The pressure that had been building in your stomach once again reaches the tipping point.

Dean buries his face into the crook of your neck as your back arches from the bed. “Dean,” you moan as your walls begin to flutter around him. His hips buck at the feeling, his rhythm faltering.

“Oh, Y/N,” Dean groans, his cock twitching hard inside you. The sensation is enough to drive you over the edge.

“Dean!” you cry out as your walls clamp down around him. Your arms tighten around him, desperate to feel his body against your own. Pleasure washes over you in waves as your body shudders. Dean captures your lips, muffling the sounds you make as he continues thrusting.

“Y/N,” Dean groans. He works himself towards his own high and helps you to ride out your own. “Oh, yes, Y/N!” Dean shouts, following you into the blissful abyss. You moan as his cock pulses inside you, spilling himself into the condom. Dean’s thrusts slow but don’t stop and you lift your hips for him, helping him through his high just as he had done for you. “Y/N,” Dean whispers as he places butterfly kisses across your face and chest.

“Dean,” you giggle back, carding your hands through his soft hair as you squirm beneath him.

Slowly, he pulls himself from you and moves to your side, leaving you achingly empty. He rids himself of the condom before wrapping you up in his arms, pulling you against him so that your back is pressed flush to his chest. “Was it everything you wanted your first time to be?” Dean asks, brushing your hair back behind your ear before pressing a kiss to your cheek.

“Even better,” you admit.

“Good,” Dean says, continuing to place random kisses across your shoulder.

“Was I alright?” you question, hoping you were as good for him as he was for you.

“Alright?” Dean asks as he intertwines the fingers of one of his hands with yours, “Y/N, you were freakin’ awesome.” He brings your hand to his lips and kisses your knuckles.

“I was?” you ask.

“Absolutely,” he answers, wrapping you tighter in his arms, “I love you and you’re nothing less than perfect.” You can’t help but smile as you look at him over your shoulder.

“I love you too,” you reply, smiling against his lips as he leans in to kiss you.


End file.
